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No man's life and work should be based on the ethics and morality of his employer, especially when the employer was the controversial leader of American Blacks in the late-nineteenth and early twentieth centuries Booker T. Washington (BTW). In the groundbreaking biographies written by Louis Harlan about BTW, that is what happened to Melvin Chisum's life. While black historians and journalists wrote about Chisum as charismatic and idiosyncratic during his lifetime; in the 1970s historian Harlan used Chisum's life story in juxtaposition to BTW's, in order to highlight the work ethic he thought BTW portrayed. Calling Chisum no more than a villainous "spy" and "provocateur" of the era, Harlan left historians and their students with a void in Progressive Era history because Chisum represented so much more in social and political endeavors during his lifetime. This dissertation uses Harlan's own achieved records, the insight of Chisum's family members, and personal letters between Chisum and colleagues. While this dissertation does not describe all of Chisum's deeds during his lifetime, it does give an overview of Harlan's perceptions, a background of Chisum's early life, corrects myths, offers a black social gospel perspective of Chisum, and fills gaps in historiography. This dissertation describes and enhances both black history and American history. Unknown inter and intra race alliances are revealed that were once thought of as unheard of in American history. Chisum's Pilgrimage II places the end of BTW's administration of accommodation, which Harlan believed ended in 1916, squarely in President Franklin Delano Roosevelt's New Deal Administration. Groundbreaking research shows that Chisum, once a spy for the American black leader BTW, became an investigator for the Public Works Administration for two consecutive terms of the New Deal. From there the dissertation briefly indicates of how Bookerites like Chisum supported the Civil Rights movement by backing the National Association for the Advancement of Colored People (NAACP).